On February 10, 1961, FBI Director J. Edgar Hoover sent a pointed memo to United States Attorney General
Robert F. Kennedy, regarding singer Frank Sinatra’s extensive connections to organized crime figures.
It was a classic Hoover move. Information had always been Hoover’s best weapon, and in Sinatra’s case the
director had stockpiled plenty of ammunition. Special agents had been keeping tabs on the singer since 1947 when he
took a four-day trip to Havana and painted the town red with a gaggle of powerful Cosa Nostra members who had gathered there
for a mob conference. Hoover’s unstated message to the attorney general in that memo was as subtle as a sledgehammer:
Look who your brother the president has been hanging around with. In fact, Sinatra had been an avid supporter of John
F. Kennedy in the 1960 presidential election, and they had become quite close.

In the memo Hoover gave a précis of Sinatra’s alleged criminal background prior to his Mafia involvement.
Hoover wrote that in 1944, according to “an anonymous complaint,” Sinatra had paid $40,000 to get out of the draft.
The FBI director went on to point out that Sinatra had “reportedly been associated with or lent his name to sixteen
organizations which have been cited or described as communist fronts” even though the bureau’s investigation never
uncovered sufficient evidence to prove that Sinatra was ever a Communist Party member himself.

Hoover then ticked off Sinatra’s criminal associates, including Joseph and Rocco Fischetti, who
were cousins of Al Capone; New Jersey crime boss Willie Moretti; James Tarantino who was himself an associate of gangster
Bugsy Siegel; Mickey Cohen of Los Angeles; and reigning Chicago boss Sam Giancana. According to Hoover, when Giancana
had been arrested in 1958, the police found Sinatra’s private telephone number in Giancana’s wallet. Hoover
described a command performance by Sinatra and singer Dean Martin at the home of “notorious Chicago hoodlum” Anthony
“Joe Batters” Accardo. According to Hoover, in the summer of 1959, Sinatra allegedly hosted a nine-day,
round-the-clock party at the Claridge Hotel in Atlantic City where Chicago wiseguys rubbed elbows with top East Coast mobsters,
including Vito Genovese and Tommy Lucchese. Hoover even quoted a female informant who had met Sinatra and Joe Fischetti
at the Hotel Fontainebleau in Miami and believed that the singer had “’a hoodlum complex.’”

Charges like these plagued Frank Sinatra throughout his life, and he repeatedly and vehemently denied
having any formal association with the Mafia. But Hoover hadn’t pulled these names out of thin air. Even
if Sinatra wasn’t a criminal himself, he certainly knew plenty of criminals and considered many of them good friends.
Despite his denials, year after year, evidence piled up indicating that Sinatra enjoyed a very special relationship with the
Mafia.

When police in Naples, Italy, searched Lucky Luciano’s home several years after the Havana getaway,
they found a gold cigarette case with the inscription, “To my dear pal Lucky, from his friend, Frank Sinatra.”

Chicago boss Sam Giancana was known to wear a star-sapphire pinkie ring that was a gift from Sinatra.

The press had published damning photographs of Sinatra posing with known Mafia members.

In conversations secretly taped by the government, gangsters mentioned Sinatra’s name frequently,
and not only with regard to his singing and acting talents.

Nevertheless, the singer continued to complain that he was being unfairly tarred with the organized-crime
brush simply because he occasionally happened to meet someone who had a criminal record or because his last name “ended
in a vowel.”

But the record shows that Sinatra’s relationships with known mob figures were often more than just
casual meetings with fans. He performed in clubs and theaters controlled by the Mafia. He made investments with
mobsters. He used his status as a celebrity to make requests on their behalf—all the way to the Oval Office in
one instance. He hosted men of honor at his home, at his hotels, even at his mother’s home. He apparently
valued their company as much as they valued his, and if he publicly chafed at being tarred with the Mafia brush, he often
used his gangland veneer to instill fear and respect on his late-night romps in the “wee small hours of the morning.”

But what exactly was Frank Sinatra’s relationship with the Mafia? Was he so respected and
revered by the wiseguys that they considered him one of their own? Was he actually an inducted member of the secret
criminal society? Or was he simply used by mobsters for their own purposes as they used so many others? Was Sinatra
a Mafia groupie, taken in by the aura of power and invincibility, intoxicated by the association? Was he their patron
saint? Or was he their patsy?